From indoles to 3,3′-biindolin-2-ones: copper-catalyzed oxidative homocoupling of indoles
A copper-catalyzed intermolecular oxidative homocoupling of indoles has been developed for the direct construction of valuable C3-C3 biindolyl scaffolds. Using this protocol, 3,3′-bisindolin-2-ones are obtained in good yields and with excellent chemo- and regioselectivity. The methodology shows good...
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| Veröffentlicht in: | New journal of chemistry 2019-09, Vol.43 (38), p.15153-1516 |
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| creator | Peng, Xiangjun Zeng, Yong Liu, Hai Xu, Xianyun Zhang, Minhong Liu, Qian |
| description | A copper-catalyzed intermolecular oxidative homocoupling of indoles has been developed for the direct construction of valuable C3-C3 biindolyl scaffolds. Using this protocol, 3,3′-bisindolin-2-ones are obtained in good yields and with excellent chemo- and regioselectivity. The methodology shows good functional group tolerance, allows the use of easily available inexpensive precursors, has simple operation, and can be performed under mild reaction conditions. From a retrosynthetic point of view, the strategic formation of a C-C bond
via
C(sp
3
-H)/C(sp
2
-H) dehydrogenative coupling may be useful in indole-derived pharmaceuticals and natural products. Upon screening HepG-2, SCG-7901, MDA-MB-468, MDA-MB-435 and Ishikawa cancer cell lines, compound
2s
exhibited a good inhibitory effect against HepG-2 at 10.49 ± 0.41 μM
in vitro
antitumor activities. Further studies, involving apoptosis ratio detection and cell cycle analysis, were conducted on compound
2s
.
A copper-catalyzed intermolecular oxidative homocoupling of indoles for the direct construction of valuable C3-C3 biindolyl scaffolds. |
| doi_str_mv | 10.1039/c9nj03620b |
| format | Article |
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via
C(sp
3
-H)/C(sp
2
-H) dehydrogenative coupling may be useful in indole-derived pharmaceuticals and natural products. Upon screening HepG-2, SCG-7901, MDA-MB-468, MDA-MB-435 and Ishikawa cancer cell lines, compound
2s
exhibited a good inhibitory effect against HepG-2 at 10.49 ± 0.41 μM
in vitro
antitumor activities. Further studies, involving apoptosis ratio detection and cell cycle analysis, were conducted on compound
2s
.
A copper-catalyzed intermolecular oxidative homocoupling of indoles for the direct construction of valuable C3-C3 biindolyl scaffolds.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/c9nj03620b</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Anticancer properties ; Apoptosis ; Cell cycle ; Copper ; Cycle ratio ; Dehydrogenation ; Functional groups ; Indoles ; Natural products ; Regioselectivity</subject><ispartof>New journal of chemistry, 2019-09, Vol.43 (38), p.15153-1516</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-6e2db7b81e8e32a11cdc456bde3ac44af4dfbe3a79c03c07ad471de6931593ad3</citedby><cites>FETCH-LOGICAL-c281t-6e2db7b81e8e32a11cdc456bde3ac44af4dfbe3a79c03c07ad471de6931593ad3</cites><orcidid>0000-0003-0715-7919</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Peng, Xiangjun</creatorcontrib><creatorcontrib>Zeng, Yong</creatorcontrib><creatorcontrib>Liu, Hai</creatorcontrib><creatorcontrib>Xu, Xianyun</creatorcontrib><creatorcontrib>Zhang, Minhong</creatorcontrib><creatorcontrib>Liu, Qian</creatorcontrib><title>From indoles to 3,3′-biindolin-2-ones: copper-catalyzed oxidative homocoupling of indoles</title><title>New journal of chemistry</title><description>A copper-catalyzed intermolecular oxidative homocoupling of indoles has been developed for the direct construction of valuable C3-C3 biindolyl scaffolds. Using this protocol, 3,3′-bisindolin-2-ones are obtained in good yields and with excellent chemo- and regioselectivity. The methodology shows good functional group tolerance, allows the use of easily available inexpensive precursors, has simple operation, and can be performed under mild reaction conditions. From a retrosynthetic point of view, the strategic formation of a C-C bond
via
C(sp
3
-H)/C(sp
2
-H) dehydrogenative coupling may be useful in indole-derived pharmaceuticals and natural products. Upon screening HepG-2, SCG-7901, MDA-MB-468, MDA-MB-435 and Ishikawa cancer cell lines, compound
2s
exhibited a good inhibitory effect against HepG-2 at 10.49 ± 0.41 μM
in vitro
antitumor activities. Further studies, involving apoptosis ratio detection and cell cycle analysis, were conducted on compound
2s
.
A copper-catalyzed intermolecular oxidative homocoupling of indoles for the direct construction of valuable C3-C3 biindolyl scaffolds.</description><subject>Anticancer properties</subject><subject>Apoptosis</subject><subject>Cell cycle</subject><subject>Copper</subject><subject>Cycle ratio</subject><subject>Dehydrogenation</subject><subject>Functional groups</subject><subject>Indoles</subject><subject>Natural products</subject><subject>Regioselectivity</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpFkM1KAzEUhYMoWKsb90LAnRjNTdJM404H6w9FN7pyMWSSjE5pJ2MyFevKZ_KRfBJj68_qHi4f58CH0C7QI6BcHRvVTCiXjJZrqAdcKqKYhPWUQQhCB0Juoq0YJ5QCZBJ66GEU_AzXjfVTF3HnMT_kn-8fpKyXv7ohjPjGxRNsfNu6QIzu9HTx5iz2r7XVXf3i8JOfeePnbcIfsa9-67bRRqWn0e383D66H53f5ZdkfHtxlZ-OiWFD6Ih0zJZZOQQ3dJxpAGONGMjSOq6NELoStipTzpSh3NBMW5GBdVJxGCiuLe-j_VVvG_zz3MWumPh5aNJkwZhSVCURIlEHK8oEH2NwVdGGeqbDogBafMsrcnVzvZR3luC9FRyi-eP-5fIvR11tcA</recordid><startdate>20190930</startdate><enddate>20190930</enddate><creator>Peng, Xiangjun</creator><creator>Zeng, Yong</creator><creator>Liu, Hai</creator><creator>Xu, Xianyun</creator><creator>Zhang, Minhong</creator><creator>Liu, Qian</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-0715-7919</orcidid></search><sort><creationdate>20190930</creationdate><title>From indoles to 3,3′-biindolin-2-ones: copper-catalyzed oxidative homocoupling of indoles</title><author>Peng, Xiangjun ; Zeng, Yong ; Liu, Hai ; Xu, Xianyun ; Zhang, Minhong ; Liu, Qian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-6e2db7b81e8e32a11cdc456bde3ac44af4dfbe3a79c03c07ad471de6931593ad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Anticancer properties</topic><topic>Apoptosis</topic><topic>Cell cycle</topic><topic>Copper</topic><topic>Cycle ratio</topic><topic>Dehydrogenation</topic><topic>Functional groups</topic><topic>Indoles</topic><topic>Natural products</topic><topic>Regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peng, Xiangjun</creatorcontrib><creatorcontrib>Zeng, Yong</creatorcontrib><creatorcontrib>Liu, Hai</creatorcontrib><creatorcontrib>Xu, Xianyun</creatorcontrib><creatorcontrib>Zhang, Minhong</creatorcontrib><creatorcontrib>Liu, Qian</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peng, Xiangjun</au><au>Zeng, Yong</au><au>Liu, Hai</au><au>Xu, Xianyun</au><au>Zhang, Minhong</au><au>Liu, Qian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>From indoles to 3,3′-biindolin-2-ones: copper-catalyzed oxidative homocoupling of indoles</atitle><jtitle>New journal of chemistry</jtitle><date>2019-09-30</date><risdate>2019</risdate><volume>43</volume><issue>38</issue><spage>15153</spage><epage>1516</epage><pages>15153-1516</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A copper-catalyzed intermolecular oxidative homocoupling of indoles has been developed for the direct construction of valuable C3-C3 biindolyl scaffolds. Using this protocol, 3,3′-bisindolin-2-ones are obtained in good yields and with excellent chemo- and regioselectivity. The methodology shows good functional group tolerance, allows the use of easily available inexpensive precursors, has simple operation, and can be performed under mild reaction conditions. From a retrosynthetic point of view, the strategic formation of a C-C bond
via
C(sp
3
-H)/C(sp
2
-H) dehydrogenative coupling may be useful in indole-derived pharmaceuticals and natural products. Upon screening HepG-2, SCG-7901, MDA-MB-468, MDA-MB-435 and Ishikawa cancer cell lines, compound
2s
exhibited a good inhibitory effect against HepG-2 at 10.49 ± 0.41 μM
in vitro
antitumor activities. Further studies, involving apoptosis ratio detection and cell cycle analysis, were conducted on compound
2s
.
A copper-catalyzed intermolecular oxidative homocoupling of indoles for the direct construction of valuable C3-C3 biindolyl scaffolds.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c9nj03620b</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-0715-7919</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2019-09, Vol.43 (38), p.15153-1516 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_rsc_primary_c9nj03620b |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Anticancer properties Apoptosis Cell cycle Copper Cycle ratio Dehydrogenation Functional groups Indoles Natural products Regioselectivity |
| title | From indoles to 3,3′-biindolin-2-ones: copper-catalyzed oxidative homocoupling of indoles |
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